CHEBI:32419 - gadoleic acid

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ChEBI Name gadoleic acid
ChEBI ID CHEBI:32419
Definition A 9-icosenoic acid having a cis-double bond at position 9.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H38O2
Net Charge 0
Average Mass 310.51450
Monoisotopic Mass 310.28718
InChI InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-
InChIKey LQJBNNIYVWPHFW-QXMHVHEDSA-N
SMILES CCCCCCCCCC\C=C/CCCCCCCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: MetaboLights Study
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: MetaboLights Study
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
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ChEBI Ontology
Outgoing gadoleic acid (CHEBI:32419) has role algal metabolite (CHEBI:84735)
gadoleic acid (CHEBI:32419) is a 9-icosenoic acid (CHEBI:180273)
gadoleic acid (CHEBI:32419) is conjugate acid of gadoleate (CHEBI:32420)
Incoming 1-hexadecyl-2-[(9Z)-eicosenoyl]-sn-glycero-3-phosphocholine (CHEBI:86432) has functional parent gadoleic acid (CHEBI:32419)
1-octadecyl-2-[(9Z)-eicosenoyl]-sn-glycero-3-phosphocholine (CHEBI:86438) has functional parent gadoleic acid (CHEBI:32419)
ethyl (9Z)-icosenoate (CHEBI:84864) has functional parent gadoleic acid (CHEBI:32419)
gadoleate (CHEBI:32420) is conjugate base of gadoleic acid (CHEBI:32419)
gadoleoyl group (CHEBI:32421) is substituent group from gadoleic acid (CHEBI:32419)
IUPAC Name
(9Z)-icos-9-enoic acid
Synonyms Sources
(9Z)-9-eicosenoic acid ChEBI
(9Z)-9-icosenoic acid ChEBI
(Z)-9-eicosenoic acid ChEBI
(Z)-9-icosenoic acid ChEBI
(Z)-eicos-9-enoic acid ChEBI
9(Z)-eicosenoic acid ChEBI
9c-Eicosensäure ChEBI
C20:1C ChEBI
cis-9-eicosenoic acid ChEBI
cis-9-icosenoic acid ChEBI
cis9-eicosenoic acid ChEBI
eicos-9c-enoic acid ChEBI
Eicos-9c-ensäure ChEBI
Manual Xrefs Databases
C00053190 KNApSAcK
FDB003771 FooDB
Gadoleic_acid Wikipedia
HMDB0062436 HMDB
LMFA01030084 LIPID MAPS
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Registry Numbers Types Sources
1727308 Reaxys Registry Number Reaxys
29204-02-2 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
25849082 PubMed citation Europe PMC
26593488 PubMed citation Europe PMC
29553827 PubMed citation Europe PMC
30690246 PubMed citation Europe PMC
32839421 PubMed citation Europe PMC
34299426 PubMed citation Europe PMC
35745025 PubMed citation Europe PMC
36990747 PubMed citation Europe PMC
38969662 PubMed citation Europe PMC
40492180 PubMed citation Europe PMC
IND607197922 Agricola citation Europe PMC
Last Modified
27 June 2025